反応 #46913

反応方程式

4-hydroxyphenylisothiocyanate

5-p-hydroxyphenyl-1,2-dithiole-3-thione

naproxene

hydroxybenzotriazole

DCC

→

4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate

収率 21.0%

溶媒

ethyl acetate

dimethylformamide

反応条件

後処理

1. 1
   workup.STIRRINGstirred for 1 h at 0° C. and 2 h at room temperature
2. 2
   ろ過After filtration
3. 3
   その他the filtrate was evaporated under reduced pressure
4. 4
   その他to remove the solvent
5. 5
   その他The oily residue thus obtained
6. 6
   その他the precipitate was removed
7. 7
   その他The solvent was evaporated
8. 8
   洗浄eluted with dichloromethane, from which 4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3)
9. 9
   その他was obtained (230 mg, 21% yield)

実験手順

To the solution of 1 (naproxene, 691 mg, 3 mmol) in 20 mL of dimethylformamide, hydroxybenzotriazole (446 mg, 3.3 mmol) and DCC (619 mg, 3.3 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxyphenylisothiocyanate (2; 500 mg, 3.3 mmol) was added and stirred for 1 h at 0° C. and 2 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in ethyl acetate and the precipitate was removed. The solvent was evaporated and the crude product was loaded on a silica gel open column and eluted with dichloromethane, from which 4-(isothiocyano)-phenyl 2-(2-methoxynaphthalen-6-yl)propanoate (3) was obtained (230 mg, 21% yield).

出典